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Design, Synthesis, in Vitro, and in Silico Biological Evaluations of Coumarin-Indole Hybrids As New Anti-Α-Glucosidase Agents Publisher



Niri DR1 ; Sayahi MH2 ; Behrouz S1 ; Moazzam A3 ; Mojtabavi S4 ; Faramarzi MA4 ; Larijani B3 ; Rastegar H5 ; Mohammadikhanaposhtani M4, 6 ; Mahdavi M3
Authors
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Authors Affiliations
  1. 1. Medicinal Chemistry Research Laboratory, Department of Chemistry, Shiraz University of Technology, Shiraz, Iran
  2. 2. Department of Chemistry, Payame Noor University (PNU), Tehran, Iran
  3. 3. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran
  4. 4. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
  5. 5. Cosmetic Products Research Center, Iranian Food and Drug Administration, MOHE, Tehran, Iran
  6. 6. Cellular and Molecular Biology Research Center, Health Research Institute, Babol University of Medical Sciences, Babol, Iran

Source: BMC Chemistry Published:2022


Abstract

Background: A series of coumarin-indole hybrids was synthesized as the new α-glucosidase inhibitors. The title hybrids were considered as α-glucosidase inhibitors because had two active pharmacophores against α-glucosidase: coumarin and indole. Methods: The thirteen various derivatives 4a–m were synthesized, purified, and fully characterized. These compounds were evaluated against α-glucosidase in vitro and in silico. In silico pharmacokinetic studies of the most potent compounds were also performed. Results: Most of the title compounds exhibited high anti-α-glucosidase activity in comparison to standard drug acarbose. In particular, the phenoxy derivative 4d namely 3-((1H-indol-3-yl)(3-phenoxyphenyl)methyl)-4-hydroxy-2H-chromen-2-one showed promising activity. This compound is a competitive inhibitor against α-glucosidase and showed the lowest binding energy at the α-glucosidase active site in comparison to other potent synthesized compounds and acarbose. Conclusion: Compound 4d can be a lead compound for further structural development to obtain effective and potent α-glucosidase inhibitors. © 2022, The Author(s).
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